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JP-7856777-B2 - Polyalphaolefin phenol with high para-position selectivity

JP7856777B2JP 7856777 B2JP7856777 B2JP 7856777B2JP-7856777-B2

Inventors

  • ティアン、シン
  • ベル、ジェイソン
  • アンダーソン、スティーブン

Assignees

  • アフトン・ケミカル・コーポレーション

Dates

Publication Date
20260511
Application Date
20230216
Priority Date
20220221

Claims (11)

  1. A sulfide alkylphenate comprising a polyalphaolefin-substituted crosslinked hydroxyaromatic compound or a salt thereof, wherein the polyalphaolefin is derived from one or more C6-C14 monomers that form an oligomer in the form of a dimer, trimer, tetramer, pentamer or combination thereof, or a copolymer or combination thereof of the oligomer, and 40 mole percent or more of the polyalphaolefin contains carbon atoms configured to form a tertiary carbocation arranged to react with the hydroxyaromatic compound at the para position, and the polyalphaolefin contains more than 40 mole percent of vinylidene olefin, trisubstituted olefin, or a mixture thereof . Alkyl phenate sulfide comprising the polyalphaolefin in a dimer of 40% by weight or more, a trimer of 40% by weight or less, a tetramer of 20% by weight or less, and a pentamer of 5% by weight or less .
  2. The alkylphenate sulfide according to claim 1, wherein at least one alkyl group adjacent to the tertiary carbocation is an alkyl group having 1, 2, or 3 carbon atoms.
  3. The alkyl phenate sulfide according to claim 1, wherein the polyalphaolefin is obtained from C8-C12 monomers that form the oligomer in the form of the dimer, trimer, tetramer, pentamer, or combination thereof.
  4. The alkylphenate sulfide according to claim 1, wherein 50 mole percent or more of the polyalphaolefin contains carbon atoms configured to form a tertiary carbocation.
  5. The alkyl sulfide phenate according to claim 1, wherein the polyalphaolefin contains 40% by weight or more of a polyalphaolefin having an alkyl group of C3 or less adjacent to a tertiary carbocation.
  6. The alkyl sulfide phenate according to claim 1, wherein the polyalphaolefin contains a double bond having a vinylidene structure and/or a trisubstituted structure.
  7. A detergent composition comprising an alkyl phenate sulfide having the structure of formula IX, During the ceremony, Each R 24 is independently a polyalphaolefin derived from one or more C6-C14 monomers forming an oligomer in the form of a dimer, trimer, tetramer, pentamer, or combination thereof, or a copolymer or combination thereof of the oligomer, and contains a residue of a tertiary carbocation that forms the bond to the aromatic ring, wherein at least 50 mole percent of R 24 is bonded to the aromatic ring at the para position, and each R 24 independently contains 40 wt percent or more of polyalphaolefin having at least one alkyl group adjacent to the tertiary carbocation having 1, 2, or 3 carbon atoms, and R 24 contains more than 40 mole percent of vinylidene olefin, trisubstituted olefin, or a mixture thereof . R 24 is divided into dimers if it is 40% or more by weight, trimers if it is 40% or less by weight, tetramers if it is 20% or less by weight, and pentamers if it is 5% or less by weight. x is an integer from 1 to 4, A detergent composition in which M²⁺ is a divalent metal ion.
  8. The detergent composition according to claim 7, wherein each R 24 is independently formed from one or more C8-C12 monomers that form the oligomer in the form of a dimer, trimer, tetramer, pentamer , or a combination thereof.
  9. The R 24 group is derived from a mixture of oligomers having the structure of formula VI and/or oligomers having the structure of formula VII, During the ceremony, Each R11 is an alkyl group, Each of R12 , R13 , R14 , R15 , and/or R16 is either identical or different each time it appears, and independently represents hydrogen or a substituted or unsubstituted hydrocarbyl group. Only one of R17 , R18 , and R19 is hydrogen, one of the remaining two of R17 , R18 , and R19 is a substituted or unsubstituted hydrocarbyl group having 1, 2, or 3 carbon atoms, and the other of the remaining two of R17 , R18 , and R19 is a substituted or unsubstituted hydrocarbyl group. Each of R20 , R21 , R22 , and/or R23 is either identical or different each time it appears, and independently represents hydrogen or a substituted or unsubstituted hydrocarbyl group. The detergent composition according to claim 7 , wherein each n is an integer from 0 to 3, independently.
  10. A lubricating oil composition comprising the alkyl phenate sulfide described in claim 1 and one or more base oils with lubricating viscosity.
  11. A lubricating oil composition comprising the detergent composition according to claim 7 and one or more base oils having a lubricating viscosity.

Description

This disclosure generally relates to lubricating oil compositions and sulfiding additives therefor, provided from polyalphaolefin-substituted phenols and salts thereof that exhibit high para-selectivity and/or reactivity on the aromatic ring. Metal salts of alkylphenols, also known as alkylphenates, tend to be useful lubricant additives. These additives can function, for example, as detergents, friction modifiers, and/or dispersants, while when used in lubricants in automotive applications, they provide an alkaline base to assist in neutralizing acids generated during vehicle operation. Unsulfurized variants of some alkylphenates or phenols (e.g., tetrapropylenephenol or phenates with C12 alkyl substitutions) tend to be less useful and less desirable in lubricants for several reasons. Therefore, additive manufacturers strive to minimize the levels of such unsulfurized alkylphenates and/or alkylphenols in their additives. However, current methods have one or more drawbacks when attempting to minimize the level of unsulfurized alkylphenate/phenol variants when the additive is also overbasicated. While altering the alkyl substitution is one possible option, alternative alkyl substitutions on the phenol moiety also present problems in relation to overbasic lubricant detergents. Desired lubricant additives prefer alkyl substitution at the para position of the aromatic ring, primarily because such substitutions enable efficient sulfidation and overbasic detergent functionality. However, many suitable alkyl substituents from other olefins preferentially alkylate at the ortho position, which is undesirable in relation to lubricant additives. According to one embodiment, an alkylphenate sulfide comprising a polyalphaolefin-substituted crosslinked hydroxyaromatic compound or a salt thereof is described herein. In the method, the polyalphaolefin is derived from C6-C14 monomers that form dimers, trimers, tetramers, pentamers, copolymers thereof, copolymer variants thereof, or combinations thereof. In other embodiments, the alkylphenates of the preceding paragraph may be combined in any combination with one or more optional features or embodiments. These optional features or embodiments may include one or more of the following: about 40 mole percent or more of the polyalphaolefin comprises carbon atoms configured to form a tertiary carbocation; and/or at least one alkyl group adjacent to the tertiary carbocation is an alkyl group having 1, 2, or 3 carbon atoms, preferably 2 carbon atoms, most preferably 1 carbon atom; and/or the carbon atoms configured to form a tertiary carbocation are arranged to react with a hydroxyaromatic compound at the para position; and/or the polyalphaolefin is a C6-C12 monomer, preferably, that forms a dimer, trimer, tetramer, pentamer, or combination thereof. The polyalphaolefin is obtained from C8-C10 monomers that form dimers, trimers, tetramers, pentamers, or combinations thereof; and/or the polyalphaolefin comprises about 50 mole percent or more, preferably about 60 mole percent or more, more preferably about 75 mole percent or more, more preferably about 85 mole percent or more, and most preferably about 90 mole percent or more carbon atoms configured to form a tertiary carbocation; and/or the polyalphaolefin comprises vinylidene olefin, trisubstituted olefin, or a mixture thereof; and/or the polyalphaolefin comprises about 40 moles of vinylidene olefin. Containing more than 100%, about 50 mol%, about 75 mol%, or about 90 mol%; and/or, the polyalphaolefin is a trisubstituted olefin and contains about 40% by weight or more dimers, preferably about 50% by weight or more dimers, more preferably about 70% by weight or more dimers; and/or, the polyalphaolefin contains about 40% by weight or less trimers, and/or about 20% by weight or less tetramers, and/or about 5% by weight or less pentamers; and/or, the polyalphaolefin is mainly vinylidene olefin, trisubstituted olefin, or mixtures thereof. The polyalphaolefin contains approximately 40% by weight or more, preferably approximately 50% by weight or more, and more preferably approximately 75% by weight or more, alkyl groups of C3 or less adjacent to the tertiary carbocation; and/or the polyalphaolefin contains a double bond having a vinylidene structure and/or a trisubstituted structure; and/or the polyalphaolefin contains approximately 40 mole percent or more, preferably approximately 60 mole percent or more, more preferably approximately 75 mole percent or more, even more preferably approximately 85 mole percent or more, and most preferably approximately 90 mole percent or more, of vinylidene olefin, trisubstituted olefin, or a combination thereof. In yet another embodiment, a detergent composition comprising an alkyl phenate sulfide having the structure of formula IX is provided herein. In the method, formula IX is... The formula comprises, where each R 24 is independently a polyalphaolefin derived from C6-C14 monomers that form a combinati